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通过环状磺酰胺亚胺与硝基亚乙烯基/二烯基 Morita-Baylis-Hillman 乙酸酯的多米诺反应来获得 4,6-二芳基吡啶酸盐。

Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita-Baylis-Hillman Acetates of Nitroolefins/Nitrodienes.

机构信息

Discipline of Chemistry, Indian Institute of Technology Indore , Simrol, Indore, 452020 Madhya Pradesh, India.

出版信息

J Org Chem. 2016 May 20;81(10):4378-85. doi: 10.1021/acs.joc.6b00472. Epub 2016 May 6.

Abstract

An interesting domino reaction of 5-membered cyclic sulfamidate imines with a variety of Morita-Baylis-Hillman acetates of nitroolefins/nitrodienes in the presence of DABCO as an organic base at 55 °C is reported for the first time. This new synthetic strategy provides a series of pharmacologically interesting 4,6-diarylpicolinates in high to excellent yields and allows several compatible functionalities on aryl rings. Moreover, the biologically interesting imidazo[1,2-a]pyridine (alpidem derivative) has been prepared in high chemical yield through a unique procedure.

摘要

首次报道了在 DABCO 作为有机碱的存在下,5-员环状磺酰胺亚胺与各种 Morita-Baylis-Hillman 硝基亚油酸酯/硝二烯的有趣的级联反应,反应温度为 55°C。这种新的合成策略提供了一系列具有药理学意义的 4,6-二芳基吡啶酸盐,产率高至优异,并允许芳环上具有多种兼容的官能团。此外,通过独特的方法制备了具有生物意义的咪唑并[1,2-a]吡啶(阿普唑仑衍生物),产率高。

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